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Ammonium Chloride → 1-(2,7-Di-t-butyl-9-fluorenyl)-2-(2-methyl-1-indenyl)ethylene

HRID 612428
ノート
印刷プレビュー

反応式

HRID 612428 の反応式
[C:1]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.Br[CH2:28][CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][C:31]=1[CH3:39].[Cl-].[NH4+]>CCOCC.CCCCCC>[C:1]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:13]=3)[CH:8]([CH:28]=[CH:29][CH:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[C:31]3[CH3:39])[C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 40900822,7-Di-tert-butylfluoreneHCID 216979183-(2-Bromoethyl)-2-methylindeneHCID 178418339Butyllithium

生成物 1

HCID 537146831-(2,7-Di-t-butyl-9-fluorenyl)-2-(2-methyl-1-indenyl)ethylene収率 93.1%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
2 回
HCID 8058Hexane溶媒

実験手順

To a 100 ml four-necked flask equipped with a reflux tube, a thermometer and a dropping funnel, 2,7-di-t-butylfluorene (1.18 g, 4.22 mmol) and dehydrated ether (30 ml) were introduced. To the flask was dropwise added a hexane solution of n-butyllithium (1.67 mol/l, 2.8 ml, 4.64 mmol) at 0° C. over a period of 1 hour, followed by stirring at room temperature for 7 hours. The reaction liquid became red orange transparent. Then, the liquid was cooled to -78° C. (a yellow orange slurry), to which a solution of 3-(2-bromoethyl)-2-methylindene (1 g, 4.22 mmol) in dehydrated ether (10 ml) was dropwise added over a period of 30 minutes. Then, the temperature of the system was allowed to spontaneously rise to room temperature, followed by stirring for 15 hours. The reaction mixture gradually became a yellow slurry. The resulting yellow slurry was poured into 200 ml of a saturated ammonium chloride aqueous solution to separate an ether phase. The aqueous phase was extracted with ether (100 ml×2), and a combined organic phase was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off, and the resulting white yellow powder was reslurried with hexane (100 ml) and filtrated to obtain 1.70 g (yield: 93%) of an aimed product of a white powder.

後処理

  1. customTo a 100 ml four-necked flask equipped with a reflux tube
  2. customThe reaction liquid
  3. additionwas dropwise added over a period of 30 minutes
  4. customto spontaneously rise to room temperature
  5. stirringby stirring for 15 hours
  6. customto separate an ether phase
  7. extractionThe aqueous phase was extracted with ether (100 ml×2)
  8. dry with materiala combined organic phase was dried over anhydrous magnesium sulfate
  9. distillationThen, the solvent was distilled off
  10. filtrationfiltrated

出典と根拠

ORDレコード
ord-30aff20d048d4efe99dbe04bd3168185
出典データセット
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06004897

反応ノート

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